Methyl 3-(4-methylbenzylidene)carbazate

The title compound, C10H12N2O2, was prepared by the reaction of methyl carbazate and 4-methylbenzaldehyde. The dihedral angle between the benzene ring and the carbazate fragment is 20.86 (10)°. In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen bonds.

The title compound, C 10 H 12 N 2 O 2 , was prepared by the reaction of methyl carbazate and 4-methylbenzaldehyde. The dihedral angle between the benzene ring and the carbazate fragment is 20.86 (10) . In the crystal structure, molecules are linked by intermolecular N-HÁ Á ÁO hydrogen bonds.

D-HÁ
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2684).  (Cimerman, et al., 1997). As part of our search for new Schiff base compounds we synthesized the title compound (I), and describe its structure here.
The molcular structure of (I) is shown in Fig. 1 (Girgis, 2006). In the crystal structure, molecules are linked by intermolecular N-H···O hydrogen bonds.

Experimental
A mixture of methyl carbazate (0.1 mol), and 4-methylbenzaldehyde (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.085 mol, yield 85%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement
H atoms were fixed geometrically and allowed to ride on their attached atoms, with C-H distances = 0.93-0.97 Å; N-H = 0.86Å and with U iso (H) = 1.2U eq (C,N) or 1.5U eq (C methyl ). Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.